INDEX

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Adams, Tara, 2, 5

adaptability, 232–33

agility, 13, 72

Allen, David, 128

analysis paralysis, 89, 156

Anderson, Marques, 2, 6, 115

antifragile, 25, 238

Anzman, Melissa, 188

assumptions: hypothesis versus, 142

asymmetric upside, 149–50

bartering, 103–4

basketball analogy, 13, 226–27

Beck, Martha, 204

Belsky, Scott, 190–91

Bezos, Jeff, 199

Biali, Susan, 95

Bilanich, Bud, 3, 6

Bisong, Gigi, 156–57

board of advisors, 97–98, 100

body: and Plant stage, 47–49, 52

boiling frog, 188

Bourke, Joanna, 67

bridge income, 79–80, 81, 84, 85

Brilliance Barter, 116–17

Brown, Brené, 114–15, 117, 204

Brynjolfsson, Erik, 119

Build-Measure-Learn feedback loop, 143

Burch, Noel, 109

burn rate, 79

calfee, 101

Campbell, Joseph, 9, 173, 235

career conversations/coaching, 10, 219–21, 223–25, 226–32

career karma, 104–5

career portfolio, 66, 146, 150, 155

Career Roomba Syndrome, 186

careers

in age of app and smartphone analogy, 8–9

operating modes for, 23–25

plateaus in, 24, 190–91, 222, 226, 235, 236

Carr, Peter, 180–81

Chaloeicheep, Adam, 2, 5, 50, 51, 102, 131–32

change

and duration of pivot, 15

fear of, 8–9, 119

and mindset, 20, 22, 23

as opportunity, 20, 22

childhood interests, 67–68

Chödrön, Pema, 10

Clark, Dorie, 126

Clow, Julie, 3, 6–7, 127, 224

collective brainpower, 94

Colvin, Geoff, 120

combinatory play and hobbies, 110–11

comfort zone, 27–28, 47, 60, 89, 111, 118, 158, 194, 197, 238

complexity, 235–39

connecting the dots, and looking backward, 10–13

Connolly, Bill, 47, 147

continuous pivot, 211–12

Cotton, Becky, 187–88, 220, 221

courage: and Launch stage, 173–95

Covey, Stephen R., 39

Dahl, Marisol, 154–55

Danckert, James, 20

Danylchuk, Lisa, 105

date-based timing, 174, 176–78

Deaton, Angus, 19

decision fatigue (ego depletion), 49–50, 52

decision

to launch, 172, 174-82, 185, 209

as separate from difficult conversations, 205–6

Decision Tracker (exercise), 166

Decoda, Tara, 181–82

Deffley, Andrew, 75, 76, 98, 99

difficult conversations, 205–6

diminishing returns, 186, 188–91

discoverable, 89–90, 123–37

Dizon, Melani, 145

Doucette, Elisa, 102, 158

Downing effect (illusory superiority), 118

drafting, career, 98–99

“Drop the Bucket” game, 114

Durand, Kyle, 2, 6, 22, 155

Dweck, Carol, 19, 20

entrepreneurs: mindset of, 17

exercise(s)

linear logic, 113

listening, 117–18

meditation, 51–52

mentor, 96–97

Pivot Hexagon, 185

platform, 128–29

skills/expertise, 108

“sliding-doors” careers, 59–60

strengths, 68, 70, 128–29

success, 58–59

30-Day Decision Tracker, 166

values mining, 41–45

vision, 57–62

Zone of Genius, 70

experts, 126–27, 128–29. See also reputation; skills/expertise; thought leadership expert

failure

and courageous life, 238

definition of, 198–99

fear of, 197–213, 238

as feedback, 201–2

regret and, 198–99

and risk, 173, 180

and values, 198, 199

family, 182. See also other people

fauxspiration, 156–57

fear

of change, 8–9, 20, 119

as consuming thinking, 113

of failure, 197–213, 238

and finances, 83

FOMO (Fear of Missing Out) and, 238

FONT (Fear of Not Trying) and, 238

and mindset, 20, 23, 28, 29

Ferriss, Tim, 20, 108

Ferry, Jenny, 166

Fields, Jonathan, 114, 117

finances

and bridge income, 79–80, 81, 84, 85

burn rate and, 79

as constraint on pivot, 35

and duration of pivot, 15

and emergency fund, 78

and income-anxiety seesaw awareness, 84–85

last resort and, 237–38

mindset and, 18, 21, 26, 29–30, 83–84

and monthly nut, 77–78, 85

risk and, 76, 78, 81

runway for, 78, 79, 157, 174

and savings, 79–80

side hustles and, 80–82

and yearly nut, 78

folding: and knowing when to fold, 185–91

Frank, Thomas, 163–64

friendtors, 100–101, 146

Gaiman, Neil, 107

Garnett, Laura, 69–70

Gaspay, Nerissa, 124

Geisel, Theodor, 150–51

get scrappy, 143–44

Gillian (sister-in-law), 56–57

Give-Receive-Achieve framework, 58–59

givers, 23, 58, 94, 104–5, 116–17, 125, 126–27, 217

Gladwell, Malcolm, 60

Godin, Seth, 81

Golofaro, Christian, 21, 22, 210–11

Gower, Bob, 148–50

Gramaglia, Casey, 51, 52

Grant, Adam, 94

Grant, Alexis, 102–3

Grayeb, Jennifer, 224, 225

greener grass, 135–36

Grey, Nick, 129

Grose, Laura, 225, 232

Grosz, Stephen, 8

grounded theory, 114–15, 116, 232

Guarriello, Tom, 233

happiness, 39, 46–47, 52, 124, 135, 202–5

happiness formula, 47

Harold (grandfather), 151–52

Harris, Dan, 51

Heller, Rachel S.F., 190

Hellstrom, Travis, 21–22

Hendricks, Gay, 69

Henry, Shawn, 93, 200

high net growth, 18–30, 221, 236

high net worth, 18–30

Hill, John, 3, 6, 54

hobbies, 110–11

hotter/colder, 41, 167

hypothesis: assumptions versus, 142

illusory superiority, 118

impacters

aim/purpose of, 18, 70

and career operating modes, 68–69

characteristics of, 19–23

and courageous life, 238–39

and discoverability, 126, 132

as givers, 94

and mindset, 19–23, 24–25, 28

self-doubt of, 118–19

strengths of, 68–69

income-anxiety seesaw, 84–85

incremental pilots, 152–53

Insight Timer app, 50

instinct and intuition, 174, 179–81, 192–93, 205, 206, 237

interests: importance of, 221–23

internal mobility and programs, 229–32

intrapreneurs, 17

Jacobson, Jeff, 55

JennyBlake.me (website), 11, 23, 29, 116

jobs

disengagement from, 4

impact of technology on, 4

reasons for leaving, 219–23

See also careers

Jobs, Steve, 11, 49

John-Reader, Courtney “CJ,” 222

Jones, Brian (alias), 3, 6–7, 177–78, 235–36

Justin (client), 40–41

Kahneman, Daniel, 19

Kaufman, Josh, 108

Kelleghan, Daniel, 127–28

Kelly, Kevin, 126

Kit (friend), 81

knots, 235–36, 239

known and unknown variables, 62–63

Koenig, Lora, 102

Kondo, Marie, 128

Kotler, Steven, 114

Krishnamurti, J., 173

Krohn, Tricia, 171–72, 203–4

last resort, 237–38

Launch stage

approvals in, 182

and “being scrappy,” 143–44

benchmarks in, 17

courage and, 173–95

and evaluation of launch, 209–11

and failure, 173, 179, 180, 195, 197–213

and fear, 171, 182, 184–85, 197–213

and finances, 171, 174–76, 177, 184–85, 187, 190, 202

and other people, 174, 181–82, 202–6

overview of, 13, 14, 171–72

perfect conditions for, 207

and Pivot Scales, 194–95

progress milestones in, 174, 178–79

and risk, 173, 180, 182, 184–85, 188, 194–95, 208–9

and success, 171, 200, 209–11

launch timing criteria, 174–82, 185, 209

Lead stage

and career development, 219–33

listening during, 219–33

overview of, 15, 217

leadership

and mindset, 23

and “servant leader” perspective, 115

thought, 60, 93, 126

lean pilots, 148–49

leapfrog approach, 130–32

learning

discernment about, 119–20

and evaluation of Pilot stage, 167

failure and, 111, 201

and how to learn, 108–9

importance of, 137

levels of, 109–10

mindset and, 21, 25, 28

and MVP, 143

letting others know you are looking, 133–35

leverage existing strengths, 7, 8, 14, 29–30, 61–62, 65–73, 89, 112, 119, 128–29

Levine, Amir, 190

Life After College (Blake), 3, 11, 18, 26, 29, 45, 154

listening

active, 118

exercise about, 117–18

to gut, 135, 136

investigative, 114–18

and networking, 117

Little, Brian R., 124

Lucius Seneca, 91

make-or-break marker, 82–83

managers, career conversations with, 223–25

Marbin, Seth, 152–53

marketable skills, 71–72

Martin, Roger, 49

Martin, Steve, 18

Maslow, Abraham, 8

mastermind groups, 101–3, 146

McAfee, Andrew, 119

McCarthy, Monica, 9, 65–66

meditation, 50–52

Meitner, Amanda and Tom, 176

mentors, 94–97, 99, 100–101, 146, 232

Miceli, Carlos, 134–35

mind map, 43–44, 45, 62

mindset

abundance, 84

and finances, 18, 21, 26, 29–30, 83–84

growth, 18–30, 221, 236

pivot, 16–17

MIPs (Most Important People), 204–5

Momentum (online community), 116–17

monthly nut, 77–78, 85

Mullainathan, Sendhil, 83

MVP (minimum viable product), 143, 144, 148. See also get scrappy

Nash, Jennie, 179

networking

and bartering, 103–4

board of advisors and, 97–98, 100

collective brainpower and, 94

discoverability and, 129, 132, 133–35

and drafting, 98–99

and expanding sphere of influence, 93

friendtors and, 100–101

and letting others know you are looking, 133–35

mastermind groups and, 101–3

and mentors, 94–97, 99, 100–101

Newport, Cal, 128

Nguyen, Davis, 154

Oka, Marvin, 193

180s, 28,

one-off mentors, 94–97

operating modes, career, 23–25, 68–69, 227

opportunities

and career conversations, 228

and organizational change, 233

sources for, 91–92

organizations

changing nature of, 232–33

pilots within, 152–53

Pivot Method within, 226–29

other people

happiness of, 202–5

and letting others know you are looking, 133–35

as MIPs, 204–5

panic zone, 27–28, 163, 174, 194, 197

Pell, Dave, 129

Pennington, Casey, 133–34, 165

performance reviews, 227, 228

personality assessments, 70

Pham, Julien, 61–62, 125

Pilot stage

aim/purpose of, 14, 136, 141, 163, 167

and being wrong, 142

characteristics of, 146–150, 158

evaluation of, 161–67

and failure, 201

and fear, 158, 194

and finances, 146, 157, 162

and “getting scrappy,” 143–59

and MVP, 143, 144

overview of, 13, 14, 141–42

and risk, 141, 145, 146, 148, 149, 151, 152, 153–55, 164–65, 171, 194

pilots

incremental, 152–53

lean, 148–49

list of common, 145

in organizations, 152–53

size of, 148–50

strong, 146-50

vision, 146

Pink, Daniel, 60

Pivot Cycle, 14, 15, 86, 138, 168, 211–12

Pivot Hexagon, 183–85

Pivot Method

aim/purpose of, 226

benefits of, 212, 217

as coaching tool, 15, 217, 229

overview and stages in, 13–17

within organizations, 226–29

pivot paradox

Don’t Push the River, 191–92

Embrace the Slow Build, 150–52

Fauxspiration, 156–57

finances and, 82, 83–84

Ignorance Is Bliss, 118–19

Make Short-Term Trade-Offs if Necessary, 183

Scarcity Versus “The Secret,” 83–84

Shoot the Moon, 208–9

When the Grass Really is Greener, 135–36

pivot points, 3, 226, 239. See also plateau, career

Pivot Scales, 194–95

PivotMethod.com, 15, 23, 50, 85, 137, 167, 213, 233

pivots/pivoting

business, 7, 15

characteristics of, 9–10

crisis compared with, 9–10

culture for, 217, 219–33

definition of, 7

degree of, 28, 161

duration of, 15

fear of, 8, 17

or getting pivoted, 4–8

mindset for, 16–17

motivation for, 1–3, 4–8

plateaus versus, 24

risk in, 9

Plant stage

aim/purpose of, 14, 35, 89, 107

finances and, 75–85

guiding principles and, 39–52

overview of, 13, 14, 35–37

project-based purpose in, 69–70, 124–25

and strengths, 35–37, 61–62, 65–73, 107, 118

values and, 35, 39–45, 52, 66

and vision, 35, 53–63, 66

plateau, career, 24, 190–91, 222, 226, 235, 236

platform, 93, 120, 125–29, 163–64, 178

progress milestones, 174, 178–79

project-based purpose, 69–70, 124–25

Project Management Triangle, 183–84

quantity/quality issues, 145, 150, 183, 228

Rapple, Rebecca, 97

Rasmussen, Christina, 10

Rath, Tom, 35–36

reciprocal transformation, 105

Redecker, Cliff, 231

redundancy, 153–55, 164

Reese, Nick, 77, 78

regret, 172, 198–99, 207, 210, 211

rejection, 130, 181–82, 195, 200

reputation

of best managers, 224

capital, 92

and discoverability, 123, 125, 127, 130

and duration of pivot, 15

networking and, 94

and strengths, 71, 72–73

results, 72

Ries, Eric, 7, 143, 148

risk

and courageous life, 238

and duration of pivot, 15

and failure, 173, 180

and finances, 76, 78, 81

incremental, 164–65

and Pivot Scales, 194–95

in pivots, 9, 17

and redundancy, 153–55

riskometer for, 27–29, 194

tolerance for, 25–27

Riskometer, 27–29, 194

Roberts, Christian, 147

Rock, Chris, 111

Rosenberg, Jonathan, 219

routines: importance of, 49

Ruiz, don Miguel, 142

runway, 78, 79, 157, 174

Sadie (client), 205–6

Sam (friend), 92

Saramago, José, 1

savings, 79–80

Scaife, John, 21, 22, 210–11

Scan stage

aim/purpose of, 14, 89–90, 115

and discoverability, 89–90, 123–37

frustration during, 136–37

and networking, 89, 91–105, 115, 132, 133–35

overview of, 13, 14, 89–90

and skills/expertise, 107–21

scarcity, 83–84

Schmidt, Eric, 77, 219

Schoenberger, Amy, 2, 5, 130

Schrotberger, Luke, 101

Seinfeld, Jerry, 161–62

Seneca, Lucius, 91

“servant leader” perspective, 115

shadowing, 95–96

Shafir, Eldar, 83

Shen, Jason, 67, 221–22

shoot-the-moon, 208–09

short-term trade-offs, 183

side hustles, 80–82, 148, 152, 165, 175, 176

Silver, Nate, 129

Sims, Stacy, 126

skills/expertise

building new, 82, 107–21

closing the gap in, 108–21

hobbies and, 110–11

marketable, 71–72, 146

technology and, 107, 119–20

transitional, 132

See also strengths

“sliding-doors” careers, 59–60

Slim, Pamela, 144

slow build (incremental) pilots, 152–53

Snow, Brooke, 62–63

Soosalu, Grant, 193

sphere of influence, 93

stagnation zone, 27–28, 194

strengths

aim/purpose of, 69–70

and career conversations, 228

and characteristics of strong pilot, 146–48

and finances, 82

leveraging existing 7, 8, 14, 29–30, 61–62, 65–73, 89, 112, 119, 128–29

and marketable skills, 71–72

mining failure for, 201–2

reputation and, 71, 72–73

and results, 72

and timing of pivots, 17

and work-history highlights, 70–73

See also skills/expertise

stretch zone, 27–28, 55, 158, 163, 180, 194, 197

structured annual career conversations, 227–29

success

Career Karma and, 104–5

defining, 58–59

mindset and, 23

rejection as stepping stone to, 200

“white picket fence” ideal of, 118–19

Sullivan, Stacy, 152

sweet spots, 23, 26–27, 68, 69

Taleb, Nassim Nicholas, 25, 149

talent, 20, 23, 67–70, 71, 147, 161, 223–24, 232. See also strengths

technology, 4, 107, 119–20

“then what” questions, 112–13

thinking

fear as consuming, 113

linear, 111–13, 176

stagnant, 157–59

strategic, 119–20

thought leadership, 60, 93, 126

Tierney, John, 49

Tom (brother), 95–96, 101, 208–9

travel pilots, 157–59

tyranny of the hows and the whole how, 55–56, 113

Uhrig, Scott, 4

unrealized gains, 186, 187–88, 189–91

Ursillo, Dave, 201–2

values

aim/purpose of, 39–40, 53

career conversations and, 228

clarification of, 39–45

clusters of, 43

ranking of, 44, 45

shifting of, 40

vision and, 53, 57

visual reminder of, 45

Vice, Roxanne, 207–9

vision

aim/purpose of, 53–55

clarification of, 60, 62–63

as cloudy, 56–57

importance of, 53–55

and knowns/unknowns, 62–63

and leapfrog approach, 132

one-year statement of, 57, 58–59, 60–62, 66

and purpose, 124

time-range for, 54–55

values and, 53, 57

Waitzkin, Josh, 108

Walker, Alice, 161

warm connections, 92. See also networking

Watson, Thomas, 65

Watts, Alan, 119

Weiss, Ronnie Mae, 223, 224–25

White, Ryan (aka Bob Gower), 148–50

why: defining your project-based purpose, 124–25

Whyte, David, 54

willpower, 48, 49

work history, 70–73

Wrzesniewski, Amy, 20–21

yearly nut, 78

“Yes, and” technique, 112, 113

Zomick, Brad, 186

Zone of Genius, 67, 68–70, 72